Where to eat

Manny's Cafeteria and DeliPosted by itslaOne of the best delis in the world and it's been open since 1942. Great pastrami and corned beef. Frequented by fireman, policemen and a diverse cross-section of real Chicagoans.

Tre Kronor Swedish RestaurantPosted by CboydThis charming little cafe is one of those places Chicagoans take guests to, because they love it so much themselves. Well-known for tasty breakfasts and lunches, but their delicious dinners are one of the best-kept secrets in the city. Expect long waits for breakfast or lunch on the weekends, but at night, you'll find it sparsely populated.

Where to drink

J Bar at the JamesPosted by travelatorIf you're looking for a post-dinner drink or two, the J Bar at The James is a good place to start. In harmony with the rest of the hotel, it's sleek, sophisticated and very cool. The barmen fashion martinis with olive lollipops (so you can look like Kojak for the night) and the waiters provide appetizers from David Burke's in-house restaurant. If you get there early enough, you might also get a seat on the attractive low-slung banquettes.

The TerracePosted by pmorganOn a weekend in Chicago with my fiancee, we discovered The Terrace at the Conrad. You snuggle up on a sofa five stories above the rest of the world but feel like you're a million miles away, so it's perfect either for romantic drinks or for a relaxed night with friends (and not as pretentious as a lot of other bars we tried in the city). The unique cocktail menu was a really big hit with my other half and even I was a fan of the 'TerraceTini'. Go in the summer and soak up the atmosphere.

Where to sleep

The BlackstonePosted by LissymoreIt's a bit out of the way, being down by Grant's Park, but the Blackstone is a lovely boutique hotel - it steps you back in time (founded in 1910) but has a really modern interior. Bright stripy carpets and massive chandeliers. Our room had a great view over the lake. Downstairs, there was a gorgeous tapas restaurant which served an amazing fig and prosciutto salad - perfect after all those deep pan Chicago pizzas.

The PeninsulaPosted by travelatorIf you're after old-world charm, I can strongly recommend The Peninsula. Located in the middle of Chicago's Magnificent Mile of department stores and designer boutiques, the Peninsula has a fabulous grand lobby and is home to Shanghai Terrace – arguably Chicago's finest Chinese restaurant. The lobby lounge is lit by 20ft-high windows, and the bar, in contrast, is intimate and low-lit, with a roaring fireplace and a surprisingly hip crowd.

What to do

Goose Island Clybourn BreweryPosted by MiffersIt is the biggest of two Goose Island pubs in Chicago and is the only place - apart from the main brewery site at 1800 West Fulton St - where the beer is brewed. Goose Island is Chicago's only "craft beer" (ie microbrewery) and has been going since 1988. They do brewery tours at the North Clybourn site on Sunday afternoons at $3 for a tour, full beer tastings and a souvenir glass to take away! It's ideal to have a leisurely lunch there (the food is also great, especially the burgers) followed by the tour.

Hyde ParkPosted by MunnThe Hyde Park area (used to be an independent town a hundred or so years ago) is an urban village with the University of Chicago as a hub. Especially see the Rockefeller Chapel, a lovely Gothic building with a magnificent organ and a bell tower that has free summer concerts. On their website you can check out events held there, too. Hyde Park has a number of bookstores - the most interesting to me are the Seminary Coop Bookstore, which sells new books, and Powell & O'Gara's, which is a maze of used books for you to get lost in.

See the skyscrapers by boatPosted by sophster76Make sure you catch a morning flight to Chicago - you'll arrive in time to catch an afternoon architecture tour of the city by river boat. Chicago's the home of the skyscraper, and you get some awesome views of some of the world's first, and finest, tall buildings from the river. From Trump Tower to the Wrigley dynasty's HQ, you'll feel like you know the city a lot better at the end of the tour. The guides are great - typically friendly Mid-Westerners keen to share their enthusiasm for one of the world's great cities.

The Cultural CentrePosted by CboydOne of the city's least-know jewels, despite being housed in the grandest piece of classical architecture on one of the busiest stretches of Michigan Avenue. An unusual thing in America, the whole place is free to the public. It is primarily a museum and performance space, with a busy schedule of exhibits and performances. On Saturdays, they often have midday dance classes for young and old (great fun, even if you just watch). The Chicago Symphony and Opera both offer free performances in the opulent Preston Bradley Hall, covered in glass mosaic, beneath the world's largest Tiffany dome. On Michigan Avenue, at Randolph. Half a block away from the Loop trains, served by several buses and underground garages;